Phthalimide → HCID 71283229, compound

HRID 335340Notes

Reaction equation

HRID 335340 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7]O)[CH2:4][CH2:3]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[CH3:9][C:2]1([CH3:1])[O:6][C@H:5]([CH2:7][N:33]2[C:29](=[O:39])[C:30]3[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:32]2=[O:34])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66643190HCID 66643190, compound

Product 1

HCID 71283229HCID 71283229, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
8 °C

Procedure

To a stirred solution of (S)-(5,5-dimethyltetrahydrofuran-2-yl)methanol (14 g, 108 mmol) and PPh3 (33.8 g, 129 mmol) in THF (140 ml) under N2 was added phthalimide (17.40 g, 118 mmol) to give a suspension. The mixture was cooled to 8° C. and DIAD (27.2 ml, 140 mmol) was added dropwise over 30 mins keeping internal T<10° C. The resulting white slurry was diluted with water (100 ml) and extracted with EtOAc (100 ml). The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) and dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane afforded the title compound as a white crystalline solid;

Workup

  1. customto give a suspension
  2. customT<10° C
  3. extractionextracted with EtOAc (100 ml)
  4. washThe organics were washed with sat. NaHCO3 (100 ml), brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-095c39f175cd4c2eba79a2a503bb6c49
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

Loading…